Certain imidazo [1,2-c]pyrimidines are known to the art.
Noell et al., J. Heterocyclic Chem., 1, 34 (1964), prepared 2,7-dichloro-5-methylthioimidazo-[1,2-c]pyrimidine, 2,5,7-trichloroimidazo[1,2-c]pyrimidine and 2,7-dihydroxy-5-methylthioimidazo[1,2-c]pyrimidine.
Kluge, J. Heterocyclic Chem., 15, 119 (1978), prepared 8-bromomethyl-5-methylimidazo[1,2-c]pyrimidine hydrobromide, 8-hydroxymethyl-5-methylimidazo[1,2-c]-pyrimidine, 1-[(5-methylimidazo[1,2-c]pyrimidine-8-yl)-methyl]-2-methylpyridinium bromide hydrobromide, 8-phenylimidazo[1,2-c]pyrimidine and 8-(4-chlorophenyl)-imidazo[1,2-c]pyrimidine. Those compounds were prepared as coccidiostats.
Coburn et al, J. Heterocyclic Chem., 19, 567 (1982), prepared certain imidazo[1,2-c]pyrimidine-2,7-diones.
Turner, U.S. Pat. No. 4,153,695, prepared certain 2,3-dihydroimidazo[1,2-c]pyrimidines substituted by hydrogen, methyl or phenyl substituents in the 2-, 3- and 8-positions; C.sub.1 -C.sub.5 alkyl, phenylamino or methylmercapto in the 5-position; and chloro, pyrrolidino, methylamino or N-methylbenzylamino in the 7-position. These compounds are said to be antiviral agents.
Yanai et al, Yakagaku Zasshi, 94(12), 1503-1514 (1974), prepared imidazo[1,2-c]pyrimidine substituted by chloro in the 7-position, or by oxo in the 5-position and hydrogen or methyl in the 7-position.
Schmidt et al, J. Heterocyclic Chem., 7, 715 (1970), prepared 2,7-dichloroimidazo[1,2-c]pyrimidine substituted by chloro, methoxy, methylthio, amino, methylamino or dimethylamino in the 5-position.
Bartholomew et al, J. Org. Chem., 40, 3708 (1975), prepared 2,7-dichloroimidazo[1,2-c]pyrimidin-5-one nucleosides.
In West German Offenlegungsschrift No. 2511316 (laid-open on Sept. 18, 1975), the company Eisai KK has disclosed various 7-hydroxyimidazo[1,2-c]pyrimidines substituted by lower alkyl, unsubstituted phenyl, nitro-substituted phenyl, methylsulphonyl or methoxycarbonyl in the 2-position; and -SR, wherein R is lower alkyl, lower alkenyl or aralkyl in the 5-position. These compounds are said to be anti-inflammatory agents.
Baker et al., J. Org. Chem., 19, 1793-1800 (1954), discloses the compound 4-amino-2-methylthio-6-(1-piperidino)pyrimidine as an intermediate in purine synthesis.